DD288385A5 - Verfahren zur herstellung von aromatischen polyhydroxyaminen - Google Patents

Verfahren zur herstellung von aromatischen polyhydroxyaminen Download PDF

Info

Publication number: DD288385A5
Authority: DD; German Democratic Republic
Prior art keywords: aromatic; compounds; general formula; mol; optionally
Prior art date: 1988-10-12

Application number

DD89333472A

Other languages

German (de)

English (en)

Inventor

Urs Thiery

Dieter Sanders

Dieter Dietrich

Gerhard Groegler

Helmut Reiff

Original Assignee

��@��k��

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-10-12

Filing date

1989-10-10

Publication date

1991-03-28

1989-10-10 Application filed by ��@��k�� filed Critical ��@��k��

1991-03-28 Publication of DD288385A5 publication Critical patent/DD288385A5/de

Links

238000004519 manufacturing process Methods 0.000 title claims description 4
238000000034 method Methods 0.000 claims abstract description 35
150000001875 compounds Chemical class 0.000 claims abstract description 34
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
-1 aminophenoxy Chemical group 0.000 claims abstract description 16
238000002360 preparation method Methods 0.000 claims abstract description 13
229920003023 plastic Polymers 0.000 claims abstract description 11
239000004033 plastic Substances 0.000 claims abstract description 11
239000004814 polyurethane Substances 0.000 claims abstract description 11
229920002635 polyurethane Polymers 0.000 claims abstract description 11
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 40
125000003118 aryl group Chemical group 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 7
239000012948 isocyanate Substances 0.000 claims description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
150000002513 isocyanates Chemical class 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000003444 phase transfer catalyst Substances 0.000 claims description 4
238000003786 synthesis reaction Methods 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
239000012433 hydrogen halide Substances 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000007858 starting material Substances 0.000 abstract description 10
230000001413 cellular effect Effects 0.000 abstract description 4
239000006260 foam Substances 0.000 abstract description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 15
229920000570 polyether Polymers 0.000 description 12
239000007789 gas Substances 0.000 description 10
239000000203 mixture Substances 0.000 description 10
229920001451 polypropylene glycol Polymers 0.000 description 10
150000001412 amines Chemical class 0.000 description 8
229920005862 polyol Polymers 0.000 description 8
150000003077 polyols Chemical class 0.000 description 8
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
229920000768 polyamine Polymers 0.000 description 6
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
229920001228 polyisocyanate Polymers 0.000 description 5
239000005056 polyisocyanate Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
239000004721 Polyphenylene oxide Substances 0.000 description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical class CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
150000002009 diols Chemical class 0.000 description 4
230000002349 favourable effect Effects 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
229920001296 polysiloxane Polymers 0.000 description 4
230000009257 reactivity Effects 0.000 description 4
239000007787 solid Substances 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
150000004714 phosphonium salts Chemical class 0.000 description 3
229920002857 polybutadiene Polymers 0.000 description 3
229920000515 polycarbonate Polymers 0.000 description 3
239000004417 polycarbonate Substances 0.000 description 3
229920000728 polyester Polymers 0.000 description 3
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
XVIRIXVOLLJIPF-UHFFFAOYSA-N 1-nitro-2-(2-nitrophenoxy)benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1OC1=CC=CC=C1[N+]([O-])=O XVIRIXVOLLJIPF-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
229910003849 O-Si Inorganic materials 0.000 description 2
229910003872 O—Si Inorganic materials 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
150000004703 alkoxides Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
239000004202 carbamide Chemical group 0.000 description 2
235000013877 carbamide Nutrition 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
230000006735 deficit Effects 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
229940117389 dichlorobenzene Drugs 0.000 description 2
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
239000000806 elastomer Substances 0.000 description 2
HNRMPXKDFBEGFZ-UHFFFAOYSA-N ethyl trimethyl methane Natural products CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
150000002334 glycols Chemical class 0.000 description 2
MWVFCEVNXHTDNF-UHFFFAOYSA-N hexane-2,3-dione Chemical compound CCCC(=O)C(C)=O MWVFCEVNXHTDNF-UHFFFAOYSA-N 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
229910052987 metal hydride Inorganic materials 0.000 description 2
150000004681 metal hydrides Chemical class 0.000 description 2
229910000000 metal hydroxide Inorganic materials 0.000 description 2
150000004692 metal hydroxides Chemical class 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000002245 particle Substances 0.000 description 2
229920001568 phenolic resin Polymers 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229920006324 polyoxymethylene Polymers 0.000 description 2
229920006295 polythiol Polymers 0.000 description 2
229920003226 polyurethane urea Polymers 0.000 description 2
238000000746 purification Methods 0.000 description 2
150000003242 quaternary ammonium salts Chemical class 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 2
229950006389 thiodiglycol Drugs 0.000 description 2
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
FQERLIOIVXPZKH-UHFFFAOYSA-N 1,2,4-trioxane Chemical compound C1COOCO1 FQERLIOIVXPZKH-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
KMAQZIILEGKYQZ-UHFFFAOYSA-N 1-chloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1 KMAQZIILEGKYQZ-UHFFFAOYSA-N 0.000 description 1
GXPIVRKDWZKIKZ-UHFFFAOYSA-N 1-fluoro-2-methyl-3-nitrobenzene Chemical compound CC1=C(F)C=CC=C1[N+]([O-])=O GXPIVRKDWZKIKZ-UHFFFAOYSA-N 0.000 description 1
PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 1
JSXAJLMUBSEJFF-UHFFFAOYSA-N 1-fluoro-3-methyl-2-nitrobenzene Chemical compound CC1=CC=CC(F)=C1[N+]([O-])=O JSXAJLMUBSEJFF-UHFFFAOYSA-N 0.000 description 1
WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
WZMOWQCNPFDWPA-UHFFFAOYSA-N 2-fluoro-4-methyl-1-nitrobenzene Chemical compound CC1=CC=C([N+]([O-])=O)C(F)=C1 WZMOWQCNPFDWPA-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical class NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
229920005830 Polyurethane Foam Polymers 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000004705 aldimines Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 1
RCTOVWPTGOZSPJ-UHFFFAOYSA-N benzyl(ethyl)azanium;chloride Chemical compound Cl.CCNCC1=CC=CC=C1 RCTOVWPTGOZSPJ-UHFFFAOYSA-N 0.000 description 1
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
239000012267 brine Substances 0.000 description 1
125000005587 carbonate group Chemical group 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000004815 dispersion polymer Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000012530 fluid Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 1
238000010559 graft polymerization reaction Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000004658 ketimines Chemical class 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
150000002605 large molecules Chemical class 0.000 description 1
239000000155 melt Substances 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
238000003408 phase transfer catalysis Methods 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000004848 polyfunctional curative Substances 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
239000011496 polyurethane foam Substances 0.000 description 1
238000010107 reaction injection moulding Methods 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000007789 sealing Methods 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000008096 xylene Substances 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
- C08G18/5027—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups directly linked to carbocyclic groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/329—Hydroxyamines containing aromatic groups
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/322—Polymers modified by chemical after-treatment with inorganic compounds containing hydrogen
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33379—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing nitro group
- C08G65/33386—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing nitro group cyclic
- C08G65/33389—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing nitro group cyclic aromatic
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2101/00—Manufacture of cellular products

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
General Chemical & Material Sciences (AREA)
Inorganic Chemistry (AREA)
Polyurethanes Or Polyureas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyamides (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

DD89333472A 1988-10-12 1989-10-10 Verfahren zur herstellung von aromatischen polyhydroxyaminen DD288385A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3834749A DE3834749A1 (de)	1988-10-12	1988-10-12	Aromatische polyhydroxypolyamine, ein verfahren zu ihrer herstellung und ihre verwendung zur herstellung von polyurethan-kunststoffen

Publications (1)

Publication Number	Publication Date
DD288385A5 true DD288385A5 (de)	1991-03-28

Family

ID=6364958

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD89333472A DD288385A5 (de)	1988-10-12	1989-10-10	Verfahren zur herstellung von aromatischen polyhydroxyaminen

Country Status (11)

Country	Link
EP (1)	EP0363758B1 (fr)
JP (1)	JPH02169614A (fr)
KR (1)	KR900006400A (fr)
AT (1)	ATE83231T1 (fr)
AU (1)	AU619903B2 (fr)
BR (1)	BR8905157A (fr)
CA (1)	CA1334104C (fr)
DD (1)	DD288385A5 (fr)
DE (2)	DE3834749A1 (fr)
ES (1)	ES2053901T3 (fr)
ZA (1)	ZA897690B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4022931A1 (de) *	1990-07-19	1992-01-23	Bayer Ag	Verfahren zur herstellung von aminophenoxygruppen aufweisenden polyethern, die nach diesem verfahren erhaltenen verbindungen und ihre verwendung als reaktionspartner fuer organische polyisocyanate
JPH05156002A (ja) *	1991-06-04	1993-06-22	Natl Starch & Chem Investment Holding Corp	ポリエーテルアミン化合物及びエポキシ系接着剤組成物
US5637119A (en) *	1995-12-29	1997-06-10	Chevron Chemical Company	Substituted aromatic polyalkyl ethers and fuel compositions containing the same
US5849048A (en) *	1997-09-30	1998-12-15	Chevron Chemical Company Llc	Substituted biphenyl poly (oxyalkylene) ethers and fuel compositions containing the same

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6038412B2 (ja) *	1982-09-21	1985-08-31	東洋ゴム工業株式会社	ポリエ−テルポリオ−ル誘導体及びその製造法
DE3622784A1 (de) *	1986-07-07	1988-01-21	Wella Ag	Neue 5-alkoxy-2,4-diamino-alkylbenzole sowie haarfaerbemittel mit 5-alkoxy-2,4-diamino-alkyl-benzolen
US4847416A (en) *	1986-10-27	1989-07-11	The Dow Chemical Company	Capping of polyols with aromatic amines
DE3713858A1 (de) *	1987-04-25	1988-11-17	Bayer Ag	Aromatische polyamine, ein verfahren zu ihrer herstellung und ihre verwendung zur herstellung von polyurethankunststoffen
EP0371248A1 (fr) *	1988-11-03	1990-06-06	Miles Inc.	Systèmes de polyurées préparés par le procédé de moulage réactif par injection

1988
- 1988-10-12 DE DE3834749A patent/DE3834749A1/de not_active Withdrawn
1989
- 1989-09-28 CA CA000613904A patent/CA1334104C/fr not_active Expired - Fee Related
- 1989-09-29 EP EP89118111A patent/EP0363758B1/fr not_active Expired - Lifetime
- 1989-09-29 AT AT89118111T patent/ATE83231T1/de not_active IP Right Cessation
- 1989-09-29 DE DE8989118111T patent/DE58902962D1/de not_active Expired - Fee Related
- 1989-09-29 ES ES89118111T patent/ES2053901T3/es not_active Expired - Lifetime
- 1989-10-09 JP JP1262315A patent/JPH02169614A/ja active Pending
- 1989-10-10 DD DD89333472A patent/DD288385A5/de not_active IP Right Cessation
- 1989-10-10 KR KR1019890014461A patent/KR900006400A/ko not_active Withdrawn
- 1989-10-10 AU AU42744/89A patent/AU619903B2/en not_active Ceased
- 1989-10-11 ZA ZA897690A patent/ZA897690B/xx unknown
- 1989-10-11 BR BR898905157A patent/BR8905157A/pt unknown

Also Published As

Publication number	Publication date
DE3834749A1 (de)	1990-04-19
ZA897690B (en)	1990-07-25
JPH02169614A (ja)	1990-06-29
AU4274489A (en)	1990-04-26
EP0363758A2 (fr)	1990-04-18
KR900006400A (ko)	1990-05-08
CA1334104C (fr)	1995-01-24
EP0363758B1 (fr)	1992-12-09
AU619903B2 (en)	1992-02-06
BR8905157A (pt)	1990-05-15
DE58902962D1 (de)	1993-01-21
ES2053901T3 (es)	1994-08-01
ATE83231T1 (de)	1992-12-15
EP0363758A3 (fr)	1991-05-02

Legal Events

Date	Code	Title	Description
1995-03-02	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0050275B1 (fr)	1983-10-19	Préparation de polyamines
EP0097290B1 (fr)	1985-04-03	Procédé en une seule étape pour la préparation de polyamines à partir de prépolymères du type NCO, polyamines et l'utilisation de ces dernières pour la production de polyuréthannes
EP0097298B1 (fr)	1986-04-30	Polyamines, procédé pour la préparation de polyamines et leur utilisation pour la préparation de polyuréthanes
DE2948419A1 (de)	1981-08-13	Verfahren zur herstellung von polyaminen und deren verwendung in einem verfahren zur herstellung von polyurethankunststoffen
DE3713858A1 (de)	1988-11-17	Aromatische polyamine, ein verfahren zu ihrer herstellung und ihre verwendung zur herstellung von polyurethankunststoffen
EP0097299B1 (fr)	1986-04-16	Polyamines, procédé pour la préparation de polyamines et leur utilisation pour la préparation de polyuréthanes
EP1448665A1 (fr)	2004-08-25	Procede de production d'alcools de polyether
DD236539A5 (de)	1986-06-11	Verwendung und herstellung von substituierten p,p'-methylen-bis-anilinen
EP0099537B1 (fr)	1986-11-05	Procédé en une étape pour la fabrication de polyamines à partir de prépolymères à groupements NCO
DE3144874A1 (de)	1983-05-19	Verfahren zur herstellung von polyaminen aus n-monoaryl-n', n'-dialkylharnstoff-verbindungen und ihre verwendung zum aufbau von polyurethanen
EP0363758B1 (fr)	1992-12-09	Polyhydroxypolyamines aromatiques, leur procédé de préparation et leur utilisation pour la préparation de résines de polyuréthane
EP0079536B1 (fr)	1987-01-21	Procédé pour la préparation de polyamines modifiées
EP0747411B1 (fr)	2003-05-02	Procédé pour la préparation de polyétherpolyols ayant des unités aromatiques
EP0045892B1 (fr)	1984-02-01	Procédé pour la préparation de précurseurs de matières plastiques contenant des noyaux oxazolin-2-one et leur utilisation dans la fabrication de matières plastiques de poids moléculaire élevé
EP0148462B1 (fr)	1987-07-08	Procédé pour la préparation in situ de diisocyanates contenant des groupes urée dans des polyols, des dispersions ou des solutions selon ce procédé et leur utilisation
EP0178525B1 (fr)	1990-10-03	Procédé pour la préparation de composés aminés à haut poids moléculaire ayant une teneur en amine monomère réduite ainsi que leur utilisation
EP0050780B1 (fr)	1983-12-28	Isocyanatooxazolinones, procédé pour la préparation de précurseurs de matières plastiques présentant le système cyclique d'oxazolinone-2 et leur utilisation pour la préparation de matières plastiques de poids moléculaire élevé
DE19914076A1 (de)	2000-09-28	Verfahren zur Herstellung von Polyurethanen
EP0353572A2 (fr)	1990-02-07	Polyisocyanates contenant des groupes urée modifiés avec des composants à longues chaînes
DE4022931A1 (de)	1992-01-23	Verfahren zur herstellung von aminophenoxygruppen aufweisenden polyethern, die nach diesem verfahren erhaltenen verbindungen und ihre verwendung als reaktionspartner fuer organische polyisocyanate
DE3824287A1 (de)	1990-02-15	N,n-disubstituierte oligo- und polyurethane, verfahren zu ihrer herstellung sowie ihre verwendung bei der herstellung von kunststoffen
EP0071138A2 (fr)	1983-02-09	Amines primaires, aromatiques et aliphatiques, contenant du soufre; procédé de préparation et utilisation dans la fabriacation de polyuréthanes